Concise Synthesis of 4-Arylquinolines via Intramolecular Cyclization of Allylamines and Ketones

The intramolecular cyclization of allylamines and ketones was achieved in the presence of potassium tert‐butoxide and N,N‐dimethylformamide. A series of 4‐arylquinolines was prepared in good yields. The reaction could be accomplished at room temperature using only a substoichiometric amount of potas...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-11, Vol.357 (16-17), p.3474-3478
Main Authors: Wei, Wen-Tao, Cheng, Ya-Juan, Hu, Yu, Chen, Yan-Yan, Zhang, Xue-Jing, Zou, Yong, Yan, Ming
Format: Article
Language:English
Subjects:
allylamines
Derivatives
Ethers
intramolecular cyclization
Ketones
N,N‐dimethylformamide
N-dimethylformamide
Potassium
potassium tert-butoxide
Quinoline
Radicals
Strategy
Synthesis
α-aminoallyl radical
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Summary:The intramolecular cyclization of allylamines and ketones was achieved in the presence of potassium tert‐butoxide and N,N‐dimethylformamide. A series of 4‐arylquinolines was prepared in good yields. The reaction could be accomplished at room temperature using only a substoichiometric amount of potassium tert‐butoxide. On the other hand, the reaction of the structurally analogous allyl ethers afforded diverse products. The reaction may proceed via the rearrangement of α‐aminoallyl radicals and the generation of nucleophilic enamine intermediates. This finding represents a new strategy for the synthesis of quinoline derivatives from readily available 2‐(allylamino)phenyl ketones.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201500647